Organic electroluminescence device and anthracene derivative

ABSTRACT

An organic electroluminescence device which comprises a cathode, an anode and an organic thin film layer comprising at least one layer comprising a light emitting layer and disposed between the cathode and the anode, wherein at least one layer in the organic thin film layer comprises an anthracene derivative having a specific structure singly or as a component of a mixture, and an anthracene derivative having a specific asymmetric structure and providing an organic electroluminescence device exhibiting a great efficiency of light emission and having a long life, are provided.

TECHNICAL FIELD

The present invention relates to an organic electroluminescence deviceand an anthracene derivative and, more particularly, to anelectroluminescence device exhibiting a great efficiency of lightemission and having a long life and an anthracene derivative providingthe device.

BACKGROUND ART

An organic electroluminescence (“electroluminescence” will beoccasionally referred to as “EL”, hereinafter) device is a spontaneouslight emitting device which utilizes the principle that a fluorescentsubstance emits light by energy of recombination of holes injected froman anode and electrons injected from a cathode when an electric field isapplied. Since an organic EL device of the laminate type driven under alow electric voltage was reported by C. W. Tang of Eastman Kodak Company(C. W. Tang and S. A. Vanslyke, Applied. Physics Letters, Volume 51,Pages 913, 1987), many studies have been conducted on organic EL devicesusing organic materials as the constituting materials. Tang et al. useda laminate structure using tris(8-hydroxyquinolinol)aluminum for thelight emitting layer and a triphenyldiamine derivative for the holetransporting layer. Advantages of the laminate structure are that theefficiency of hole injection into the light emitting layer can beincreased, that the efficiency of forming excited particles which areformed by blocking and recombining electrons injected from the cathodecan be increased, and that excited particles formed within the lightemitting layer can be enclosed. As the structure of the organic ELdevice, a two-layered structure having a hole transporting (injecting)layer and an electron transporting and light emitting layer and athree-layered structure having a hole transporting (injecting) layer, alight emitting layer and an electron transporting (injecting) layer arewell known. To increase the efficiency of recombination of injectedholes and electrons in the devices of the laminate type, the structureof the device and the process for forming the device have been studied.

As the light emitting material, chelate complexes such astris(8-quinolinolato)aluminum, coumarine derivatives,tetraphenyl-butadiene derivatives, bisstyrylarylene derivatives andoxadiazole derivatives are known. It is reported that light in thevisible region ranging from blue light to red light can be obtained byusing these light emitting materials, and development of a deviceexhibiting color images is expected (For example, Japanese PatentApplication Laid-Open Nos. Heisei 8(1996)-239655, Heisei 7(1995)-138561and Heisei 3(1991)-200289).

A device using a phenylanthracene derivative as the light emittingmaterial is disclosed in Japanese Patent Application Laid-Open No.Heisei 8(1996)-012600. This anthracene derivative is used as thematerial for emitting bluish light, but an increase in the life of thedevice have been desired. A compound having fluoranthene group at the 9-and 10-positions of anthracene is disclosed as the material for thedevice in Japanese Patent Application Laid-Open No. 2001-257074. Thiscompound is also used as the material for emitting bluish light, but anincrease in the life of the device have also been desired. It isdisclosed in Japanese Patent. Application Laid-Open No. 2000-182776 thatvarious anthracene derivatives are used as the hole transportingmaterial. However, these derivatives have not been actually synthesized,and the evaluation of these compounds as the light emitting material hasnot been made.

DISCLOSURE OF THE INVENTION

The present invention has been made to overcome the above problems andhas an object of providing an EL device exhibiting a great efficiency oflight emission and has a long life and an anthracene derivativeproviding the device.

As the result of intensive studies by the present inventors to achievethe above object, it was found that an EL device exhibiting a greatefficiency of light emission and has a long life could be obtained whena compound having an anthracene structure having a specific asymmetricstructure represented by general formula (1) or (2) shown below is usedas the light emitting material of an organic EL device. The presentinvention has been completed based on this knowledge.

The present invention provides an organic electroluminescence devicewhich comprises a cathode, an anode and an organic thin film layercomprising at least one layer comprising a light emitting layer anddisposed between the cathode and the anode, wherein at least one layerin the organic thin film layer comprises, singly or as a component of amixture, an anthracene derivative represented by general formula (1) or(2) shown in the following.

In general formula (1), Ar represents a substituted or unsubstitutedcondensed aromatic group having 10 to 50 nuclear carbon atoms;

Ar′ represents a substituted or unsubstituted aromatic group having 6 to50 nuclear carbon atoms;

X represents a substituted or unsubstituted aromatic group having 6 to50 nuclear carbon atoms, a substituted or unsubstituted aromaticheterocyclic group having 5 to 50 nuclear atoms, a substituted orunsubstituted alkyl group having 1 to 50 carbon atoms, a substituted orunsubstituted alkoxyl group having 1 to 50 carbon atoms, a substitutedor unsubstituted aralkyl group having 6 to 50 carbon atoms, asubstituted or unsubstituted aryloxyl group having 5 to 50 nuclearatoms, a substituted or unsubstituted arylthio group having 5 to 50nuclear atoms, a substituted or unsubstituted alkoxycarbonyl grouphaving 1 to 50 carbon atoms, carboxyl group, a halogen atom, cyanogroup, nitro group or hydroxyl group;

a, b and c each represent an integer of 0 to 4; and

n represents an integer of 1 to 3 and, when n represents 2 or 3, aplurality of groups in [ ] represented by:

may be a same with or different from each other.

The present invention also provides an anthracene derivative representedby following general formula (2);

wherein Ar represents a substituted or unsubstituted condensed aromaticgroup having 10 to 50 nuclear carbon atoms;

Ar′ represents a substituted or unsubstituted aromatic group having 6 to50 nuclear carbon atoms;

X represents a substituted or unsubstituted aromatic group having 6 to50 nuclear carbon atoms, a substituted or unsubstituted aromaticheterocyclic group having 5 to 50 nuclear atoms, a substituted orunsubstituted alkyl group having 1 to 50 carbon atoms, a substituted orunsubstituted alkoxyl group having 1 to 50 carbon atoms, a substitutedor unsubstituted aralkyl group having 6 to 50 carbon atoms, asubstituted or unsubstituted aryloxyl group having 5 to 50 nuclearatoms, a substituted or unsubstituted arylthio group having 5 to 50nuclear atoms, a substituted or unsubstituted alkoxycarbonyl grouphaving 1 to 50 carbon atoms, carboxyl group, a halogen atom, cyanogroup, nitro group or hydroxyl group;

a and b each represent an integer of 0 to 4; and

n represents an integer of 1 to 3 and, when n represents 2 or 3, aplurality of groups in [ ] represented by:

may be a same with or different from each other.

THE MOST PREFERRED EMBODIMENT TO CARRY OUT THE INVENTION

The organic EL device of the present invention comprises a cathode, ananode and an organic thin film layer comprising at least one layercomprising a light emitting layer and disposed between the cathode andthe anode, wherein at least one layer in the organic thin film layercomprises an anthracene derivative represented by general formula (1)shown above singly or as a component of a mixture.

In general formula (1), Ar represents a substituted or unsubstitutedcondensed aromatic group having 10 to 50 nuclear carbon atoms.

Examples of the condensed aromatic group include 1-naphthyl group,2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group,1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group,4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group,2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenylgroup, 4-pyrenyl group, 3-methyl-2-naphthyl group, 4-methyl-1-naphthylgroup and 4-methyl-1-anthryl group.

It is preferable that the group represented by Ar in general formula (1)is a group selected from groups represented by following generalformulae

wherein Ar₁ represents a substituted or unsubstituted aromatic grouphaving 6 to 50 nuclear carbon atoms.

Examples of the group represented by Ar₁ include phenyl group,1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group,9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthrylgroup, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group,2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenylgroup, 4-pyrenyl group, 2-biphenylyl group, 3-biphenylyl group,4-biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group,p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group,m-terphenyl-2-yl group, o-tolyl group, m-tolyl group, p-tolyl group,p-t-butylphenyl group, p-(2-phenylpropyl)phenyl group,3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthrylgroup, 4′-methylbiphenylyl group and 4″-t-butyl-p-terphenyl-4-yl group.

In general formula (1), Ar′ represents a substituted or unsubstitutedaromatic group having 6 to 50 nuclear carbon atoms. Examples of thearomatic group include phenyl group, 1-naphthyl group, 2-naphthyl group,1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenanthryl group,2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group,9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group,9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group,2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group,p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group,m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group,o-tolyl group, m-tolyl group, p-tolyl group, p-t-butylphenyl group,p-(2-phenylpropyl)phenyl group, 3-methyl-2-naphthyl group,4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4′-methylbiphenylylgroup and 4″-t-butyl-p-terphenyl-4-yl group.

Among these groups, substituted and substituted aromatic groups having10 or more nuclear carbon atoms such as 1-naphthyl group, 2-naphthylgroup, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group,9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group,2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, o-tolylgroup, m-tolyl group, p-tolyl group and p-t-butylphenyl group arepreferable.

In general formula (1), X represents a substituted or unsubstitutedaromatic group having 6 to 50 nuclear carbon atoms, a substituted orunsubstituted aromatic heterocyclic group having 5 to 50 nuclear atoms,a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,a substituted or unsubstituted alkoxyl group having 1 to 50 carbonatoms, a substituted or unsubstituted aralkyl group having 6 to 50carbon atoms, a substituted or unsubstituted aryloxyl group having 5 to50 nuclear atoms, a substituted or unsubstituted arylthio group having 5to 50 nuclear atoms, a substituted or unsubstituted alkoxycarbonyl grouphaving 1 to 50 carbon atoms, carboxyl group, a halogen atom, cyanogroup, nitro group or hydroxyl group.

Examples of the substituted and unsubstituted aromatic group representedby X include phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthrylgroup, 2-anthryl group, 9-anthryl group, 1-phenanthryl group,2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group,9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group,9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group,2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group,p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group,m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group,o-tolyl group, m-tolyl group, p-tolyl group, p-t-butylphenyl group,p-(2-phenylpropyl)phenyl group, 3-methyl-2-naphthyl group,4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4′-methylbiphenylylgroup and 4″-t-butyl-p-terphenyl-4-yl group.

Examples of the substituted and unsubstituted aromatic heterocyclicgroup represented by X include 1-pyrrolyl group, 2-pyrrolyl group,3-pyrrolyl group, pyradinyl group, 2-pyridinyl group, 3-pyridinyl group,4-pyridinyl group, 1-indolyl group, 2-indolyl group, 3-indolyl group,4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group,1-isoindolyl group, 2-isoindolyl group, 3-isoindolyl group, 4-isoindolylgroup, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group,2-furyl group, 3-furyl group, 2-benzofuranyl group, 3-benzofuranylgroup, 4-benzofuranyl group, 5-benzofuranyl group, 6-benzofuranyl group,7-benzofuranyl group, 1-isobenzofuranyl group, 3-isobenzofuranyl group,4-isobenzofuranyl group, 5 isobenzofuranyl group, 6-isobenzofuranylgroup, 7-isobenzofuranyl group, 2-quinolyl group, 3-quinolyl group,4-quinolyl group, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group,8-quinolyl group, 1-isoquinolyl group, 3-isoquinolyl group,4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group,7-isoquinolyl group, 8-isoquinolyl group, 2-quinoxalinyl group,5-quinoxalinyl group, 6-quinoxalinyl group, 1-carbazolyl group,2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolylgroup, 1-phenanthridinyl group, 2-phenanthridinyl group,3-phenanthridinyl group, 4-phenanthridinyl group, 6-phenanthridinylgroup, 7-phenanthridinyl group, 8-phenanthridinyl group,9-phenanthridinyl group, 10-phenanthridinyl group, 1-acridinyl group,2-aeridinyl group, 3-acridinyl group, 4-acridinyl group, 9-acridinylgroup, 1,7-phenanthrolin-2-yl group, 1,7-phenanthrolin-3-yl group,1,7-phenanthrolin-4-yl group, 1,7-phenanthrolin-5-yl group,1,7-phenanthrolin-6-yl group, 1,7-phenanthrolin-8-yl group,1,7-phenanthrolin-9-yl group, 1,7-phenanthrolin-10-yl group,1,8-phenanthrolin-2 group, 1,8-phenanthrolin-3-yl group,1,8-phenanthrolin-4-yl group, 1,8-phenanthrolin-5-yl group,1,8-phenanthrolin-6-yl group, 1,8-phenanthrolin-7-yl group,1,8-phenanthrolin-9-yl group, 1,8-phenanthrolin-10-yl group,1,9-phenanthrolin-2-yl group, 1,9-phenanthrolin-3-yl group,1,9-phenanthrolin-4-yl group, 1,9-phenanthrolin-5-yl group,1,9-phenanthrolin-6-yl group, 1,9-phenanthrolin-7-yl group,1,9-phenanthrolin-8-yl group, 1,9-phenanthrolin-10-yl group,1,10-phenanthrolin-2-yl group, 1,10-phenanthrolin-3-yl group,1,10-phenanthrolin-4-yl group, 1,10-phenanthrolin-5-yl group,2,9-phenanthrolin-1-yl group, 2,9-phenanthrolin-3-yl group,2,9-phenanthrolin-4-yl group, 2,9-phenanthrolin-5-yl group,2,9-phenanthrolin-6-yl group, 2,9-phenanthrolin-7-yl group,2,9-phenanthrolin-8-yl group, 2,9-phenanthrolin-10-yl group,2,8-phenanthrolin-1-yl group, 2,8-phenanthrolin-3-yl group,2,8-phenanthrolin-4-yl group, 2,8-phenanthrolin-5-yl group,2,8-phenanthrolin-6-yl group, 2,8-phenanthrolin-7-yl group,2,8-phenanthrolin-9-yl group, 2,8-phenanthrolin-10-yl group,2,7-phenanthrolin-1-yl group, 2,7-phenanthrolin-3-yl group,2,7-phenanthrolin-4-yl group, 2,7-phenanthrolin-5-yl group,2,7-phenanthrolin-6-yl group, 2,7-phenanthrolin-8-yl group,2,7-phenanthrolin-9-yl group, 2,7-phenanthrolin-10-yl group,1-phenazinyl group, 2-phenazinyl group, 1-phenothiazinyl group,2-phenothiazinyl group, 3-phenothiazinyl group, 4-phenothiazinyl group,10-phenothiazinyl group, 1-phenoxazinyl group, 2-phenoxazinyl group,3-phenoxazinyl group, 4-phenoxazinyl group, 10-phenoxazinyl group,2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 2-oxadiazolylgroup, 5-oxadiazolyl group, 3-furazanyl group, 2-thienyl group,3-thienyl group, 2-methylpyrrol-1-yl group, 2-methylpyrrol-3-yl group,2-methylpyrrol-4-yl group, 2-methylpyrrol-5-yl group,3-methylpyrrol-1-yl group, 3-methylpyrrol-2-yl group,3-methylpyrrol-4-yl group, 3-methylpyrrol-5-yl group,2-t-butylpyrrol-4-yl group, 3-(2-phenylpropyl)pyrrol-1-yl group,2-methyl-1-indolyl group, 4-methyl-1-indolyl group, 2-methyl-3-indolylgroup, 4-methyl-3-indolyl group, 2-t-butyl-1-indolyl group,4-t-butyl-1-indolyl group, 2-t-butyl-3-indolyl group and4-t-butyl-3-indolyl group.

Examples of the substituted and unsubstituted alkyl group represented byX include methyl group, ethyl group, propyl group, isopropyl group,n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentylgroup, n-hexyl group, n-heptyl group, n-octyl group, hydroxymethylgroup, 1-hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutylgroup, 1,2-dihydroxyethyl group, 1,3-dihydroxy-isopropyl group,2,3-dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, chloromethylgroup, 1-chloroethyl group, 2-chloroethyl group, 2-chloroisobutyl group,1,2-dichloroethyl group, 1,3-dichloroisopropyl group,2,3-dichloro-t-butyl group, 1,2,3-trichloropropyl group, bromomethylgroup, 1-bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group,1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2,3-dibromo-t-butylgroup, 1,2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group,2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group,1,3-diiodoisopropyl group, 2,3-diiodo-t-butyl group, 1,2,3-triiodopropylgroup, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group,2-aminoisobutyl group, 1,2-diaminoethyl group, 1,3-diaminoisopropylgroup, 2,3-diamino-t-butyl group, 1,2,3-triaminopropyl group,cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group,2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropylgroup, 2,3-dicyano-t-butyl group, 1,2,3-tricyanopropyl group,nitromethyl group, 1-nitroethyl group, 2-nitroethyl group,2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropylgroup, 2,3-dinitro-t-butyl group, 1,2,3-trinitropropyl group,cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexylgroup, 4-methylcyclohexyl group, 1-adamantyl group, 2-adamantyl group,1-norbornyl group and 2-norbornyl group.

The substituted and unsubstituted alkoxyl group represented by X is agroup represented by —OY. Examples of the group represented by Y includemethyl group, ethyl group, propyl group, isopropyl group, n-butyl group,s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexylgroup, n-heptyl group, n-octyl group, hydroxymethyl group,1-hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutyl group,1,2-dihydroxyethyl group, 1,3-dihydroxy-isopropyl group,3-dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, chloromethylgroup, 1-chloroethyl group, 2-chloroethyl group, 2-chloroisobutyl group,1,2-dichloroethyl group, 1,3-dichloroisopropyl group,2,3-dichloro-t-butyl group, 1,2,3-trichloropropyl group, bromomethylgroup, 1-bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group,1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2,3-dibromo-t-butylgroup, 1,2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group,2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group,1,3-diiodoisopropyl group, 2,3-diiodo-t-butyl group, 1,2,3-triiodopropylgroup, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group,2-aminoisobutyl group, 1,2-diaminoethyl group, 1,3-diaminoisopropylgroup, 2,3-diamino-t-butyl group, 1,2,3-triaminopropyl group,cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group,2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropylgroup, 2,3-dicyano-t-butyl group, 1,2,3-tricyanopropyl group,nitromethyl group, 1-nitroethyl group, 2-nitroethyl group,2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropylgroup, 2,3-dinitro-t-butyl group and 1,2,3-trinitropropyl group.

Examples of the substituted and unsubstituted aralkyl group representedby X include benzyl group, 1-phenylethyl group, 2-phenylethyl group,1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group,α-naphthylmethyl group, 1-α-naphthylethyl group, 2-α-naphthylethylgroup, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group,β-naphthylmethyl group, 1-β-naphthylethyl group, 2-β-naphthylethylgroup, 1-β-naphthylisopropyl group, 2-β-naphthylisopropyl group,1-pyrrolylmethyl group, 2-(1-pyrrolyl)ethyl group, p-methylbenzyl group,m-methylbenzyl group, o-methylbenzyl group, p-chlorobenzyl group,m-chlorobenzyl group, o-chlorobenzyl group, p-bromobenzyl group,m-bromobenzyl group, o-bromobenzyl group, p-iodobenzyl group,m-iodobenzyl group, o-iodobenzyl group, p-hydroxybenzyl group,m-hydroxybenzyl group, o-hydroxybenzyl group, p-aminobenzyl group,m-aminobenzyl group, o-aminobenzyl group, p-nitrobenzyl group,m-nitrobenzyl group, o-nitrobenzyl group, p-cyanobenzyl group,m-cyanobenzyl group, o-cyanobenzyl group, 1-hydroxy-2-phenylisopropylgroup and 1-chloro-2-phenylisopropyl group.

The substituted and unsubstituted aryloxyl group represented by X is agroup represented by —OY′. Examples of the group represented by Yinclude phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthrylgroup, 2-anthryl group, 9-anthryl group, 1-phenanthryl group,2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group,9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group,9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group,2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group,p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group,m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group,o-tolyl group, m-tolyl group, p-tolyl group, p-t-butylphenyl group,p-(2-phenylpropyl)phenyl group, 3-methyl-2-naphthyl group,4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4′-methylbiphenylylgroup, 4″-t-butyl-p-terphenyl-4-yl group, 2-pyrrolyl group, 3-pyrrolylgroup, pyradinyl group, 2-pyridinyl group, 3-pyridinyl group,4-pyridinyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group,5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindolyl group,3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolylgroup, 7-isoindolyl group, 2-furyl group, 3-furyl group, 2-benzofuranylgroup, 3-benzofuranyl group, 4-benzofuranyl group, 5-benzofuranyl group,6-benzofuranyl group, 7-benzofuranyl group, 1-isobenzofuranyl group,3-isobenzofuranyl group, 4-isobenzofuranyl group, 5-isobenzofuranylgroup, 6-isobenzofuranyl group, 7-isobenzofuranyl group, 2-quinolylgroup, 3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6-quinolylgroup, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group,3-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group,6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group,2-quinoxanyl group, 5-quinoxanyl group, 6-quinoxanyl group, 1-carbazolylgroup, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group,1-phenanthridinyl group, 2-phenanthridinyl group, 3-phenanthridinylgroup, 4-phenanthridinyl group, 6-phenanthridinyl group,7-phenanthridinyl group, 8-phenanthridinyl group, 9-phenanthridinylgroup, 10-phenanthridinyl group, 1-acridinyl group, 2-acridinyl group,3-acridinyl group, 4-acridinyl group, 9-acridinyl group,1,7-phenanthrolin-2-yl group, 1,7-phenanthrolin-3-yl group,1,7-phenanthrolin-4-yl group, 1,7-phenanthrolin-5-yl group,1,7-phenanthrolin-6-yl group, 1,7-phenanthrolin-8-yl group,1,7-phenanthrolin-9-yl group, 1,7-phenanthrolin-10-yl group,1,8-phenanthrolin-2-yl group, 1,8-phenanthrolin-3-yl group,1,8-phenanthrolin-4-yl group, 1,8-phenanthrolin-5-yl group,1,8-phenanthrolin-6-yl group, 1,8-phenanthrolin-7-yl group,1,8-phenanthrolin-9-yl group, 1,8-phenanthrolin-10-yl group,1,9-phenanthrolin-2-yl group, 1,9-phenanthrolin-3-yl group,1,9-phenanthrolin-4-yl group, 1,9-phenanthrolin-5-yl group,1,9-phenanthrolin-6-yl group, 1,9-phenanthrolin-7-yl group,1,9-phenanthrolin-8-yl group, 1,9-phenanthrolin-10-yl group,1,10-phenanthrolin-2-yl group, 1,10-phenanthrolin-3-yl group,1,10-phenanthrolin-4-yl group, 1,10-phenanthrolin-5-yl group,2,9-phenanthrolin-1-yl group, 2,9-phenanthrolin-3-yl group,2,9-phenanthrolin-4-yl group, 2,9-phenanthrolin-5-yl group,2,9-phenanthrolin-6-yl group, 2,9-phenanthrolin-7-yl group,2,9-phenanthrolin-8-yl group, 2,9-phenanthrolin-10-yl group,2,8-phenanthrolin-1-yl group, 2,8-phenanthrolin-3-yl group,2,8-phenanthrolin-4-yl group, 2,8-phenanthrolin-5-yl group,2,8-phenanthrolin-6-yl group, 2,8-phenanthrolin-7-yl group,2,8-phenanthrolin-9-yl group, 2,8-phenanthrolin-10-yl group,2,7-phenanthrolin-1-yl group, 2,7-phenanthrolin-3-yl group,2,7-phenanthrolin-4-yl group, 2,7-phenanthrolin-5-yl group,2,7-phenanthrolin-6-yl group, 2,7-phenanthrolin-8-yl group,2,7-phenanthrolin-9-yl group, 2,7-phenanthrolin-10-yl group,1-phenazinyl cup, 2-phenazinyl group, 1-phenothiazinyl group,2-phenothiazinyl group, 3-phenothiazinyl group, 4-phenothiazinyl group,1-phenoxazinyl group, 2-phenoxazinyl group, 3-phenoxazinyl group,4-phenoxazinyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolylgroup, 2-oxadiazolyl group, 5-oxadiazolyl group, 3-furazanyl group,2-thienyl group, 3-thienyl group, 2-methylpyrrol-1-yl group,2-methylpyrrol-3-yl group, 2-methylpyrrol-4-yl group,2-methylpyrrol-5-yl group, 3-methylpyrrol-1-yl group,3-methylpyrrol-2-yl group, 3-methylpyrrol-4-yl group,3-methylpyrrol-5-yl group, 2-t-butylpyrrol-4-yl group,3-(2-phenylpropyl)pyrrol-1-yl group, 2-methyl-1-indolyl group,4-methyl-1-indolyl group, 2-methyl-3-indolyl group, 4-methyl-3-indolylgroup, 2-t-butyl-1-indolyl group, 4-t-butyl-1-indolyl group,2-t-butyl-3-indolyl group and 4-t-butyl-3-indolyl group.

The substituted and unsubstituted arylthio group represented by X is agroup represented by —SY″. Examples of the group represented by Y″include phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthrylgroup, 2-anthryl group, 9-anthryl group, 1-phenanthryl group,2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group,9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group,9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group,2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group,p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group,m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group,o-tolyl group, m-tolyl group, p-tolyl group, p-t-butylphenyl group,p-(2-phenylpropyl)phenyl group, 3-ethyl-2-naphthyl group,4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4′-methylbiphenylylgroup, 4″-t-butyl-p-terphenyl-4-yl group, 2-pyrrolyl group, 3-pyrrolylgroup, pyradinyl group, 2-pyridinyl group, 3-pyridinyl group,4-pyridinyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group,5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindolyl group,3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolylgroup, 7-isoindolyl group, 2-furyl group, 3-furyl group, 2-benzofuranylgroup, 3-benzofuranyl group, 4-benzofuranyl group, 5-benzofuranyl group,6-benzofuranyl group, 7-benzofuranyl group, 1-isobenzofuranyl group,3-isobenzofuranyl group, 4-isobenzofuranyl group, 5-isobenzofuranylgroup, 6-isobenzofuranyl group, 7-isobenzofuranyl group, 2-quinolylgroup, 3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6-quinolylgroup, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group,3-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group,6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group,2-quinoxalinyl group, 5-quinoxalinyl group, 6-quinoxalinyl group,1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolylgroup, 1-phenanthridinyl group, 2-phenanthridinyl group,3-phenanthridinyl group, 4-phenanthridinyl group, 6-phenanthridinylgroup, 7-phenanthridinyl group, 8-phenanthridinyl group,9-phenanthridinyl group, 10-phenanthridinyl group, 1-acridinyl group,2-acridinyl group, 3-acridinyl group, 4-acridinyl group, 9-acridinylgroup, 1,7-phenanthrolin-2-yl group, 1,7-phenanthrolin-3-yl group,1,7-phenanthrolin-4-yl group, 1,7-phenanthrolin-5-yl group,1,7-phenanthrolin-6-yl group, 1,7-phenanthrolin-8-yl group,1,7-phenanthrolin-9-yl group, 1, 7-phenanthrolin-10-yl group,1,8-phenanthrolin-2-yl group, 1,8-phenanthrolin-3-yl group,1,8-phenanthrolin-4-yl group, 1,8-phenanthrolin-5-yl group,1,8-phenanthrolin-6-yl group, 1,8-phenanthrolin-7-yl group,1,8-phenanthrolin-9-yl group, 1,8-phenanthrolin-10-yl group,1,9-phenanthrolin-2-yl group, 1,9-phenanthrolin-3-yl group,1,9-phenanthrolin-4-yl group, 1,9-phenanthrolin-5-yl group,1,9-phenanthrolin-6-yl group, 1,9-phenanthrolin-7-yl group,1,9-phenanthrolin-8-yl group, 1,9-phenanthrolin-10-yl group,1,10-phenanthrolin-2-yl group, 1,10-phenanthrolin-3-yl group,1,10-phenanthrolin-4-yl group, 1,10-phenanthrolin-5-yl group,2,9-phenanthrolin-1-yl group, 2,9-phenanthrolin-3-yl group,2,9-phenanthrolin-4-yl group, 2,9-phenanthrolin-5-yl group,2,9-phenanthrolin-6-yl group, 2,9-phenanthrolin-7-yl group,2,9-phenanthrolin-8-yl group, 2,9-phenanthrolin-10-yl group,2,8-phenanthrolin-1-yl group, 2,8-phenanthrolin-3-yl group,2,8-phenanthrolin-4-yl group, 2,8-phenanthrolin-5-yl group,2,8-phenanthrolin-6-yl group, 2,8-phenanthrolin-7-yl group,2,8-phenanthrolin-9-yl group, 2,8-phenanthrolin-10-yl group,2,7-phenanthrolin-1-yl group, 2,7-phenanthrolin-3-yl group,2,7-phenanthrolin-4-yl group, 2,7-phenanthrolin-5-yl group,2,7-phenanthrolin-6-yl group, 2,7-phenanthrolin-8-yl group,2,7-phenanthrolin-9-yl group, 2,7-phenanthrolin-10-yl group,1-phenazinyl group, 2-phenazinyl group, 1-phenothiazinyl group,2-phenothiazinyl group, 3-phenothiazinyl group, 4-phenothiazinyl group,1-phenoxazinyl group, 2-phenoxazinyl group, 3-phenoxazinyl group,4-phenoxazinyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolylgroup, 2-oxadiazolyl group, 5-oxadiazolyl group, 3-furazanyl group,2-thienyl group, 3-thienyl group, 2-methylpyrrol-1-yl group,2-methylpyrrol-3-yl group, 2-methylpyrrol-4-yl group,2-methylpyrrol-5-yl group, 3-methylpyrrol-1-yl group,3-methylpyrrol-2-yl group, 3-methylpyrrol-4-yl group,3-methylpyrrol-5-yl group, 2-t-butylpyrrol-4-yl group,3-(2-phenylpropyl)pyrrol-1-yl group, 2-methyl-1-indolyl group,4-methyl-1-indolyl group, 2-methyl-3-indolyl group, 4-methyl-3-indolylgroup, 2-t-butyl-1-indolyl group, 4-t-butyl-1-indolyl group,2-t-butyl-3-indolyl group and 4-t-butyl-3-indolyl group.

The substituted and unsubstituted alkoxycarbonyl group represented by Xis a group represented by —COOZ. Examples of the group represented by Zinclude methyl group, ethyl group, propyl group, isopropyl group,n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentylgroup, n-hexyl group, n-heptyl group, n-octyl group, hydroxymethylgroup, 1-hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutylgroup, 1,2-dihydroxyethyl group, 1,3-dihydroxy-isopropyl group,2,3-dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, chloromethylgroup, 1-chloroethyl group, 2-chloroethyl group, 2-chloroisobutyl group,1,2-dichloroethyl group, 1,3-dichloroisopropyl group,2,3-dichloro-t-butyl group, 1,2,3-trichloropropyl group, bromomethylgroup, 1-bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group,1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2,3-dibromo-t-butylgroup, 1,2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group,2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group,1,3-diiodoisopropyl group, 2,3-diiodo-t-butyl group, 1,2,3-triiodopropylgroup, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group,2-aminoisobutyl group, 1,2-diaminoethyl group, 1,3-diaminoisopropylgroup, 2,3-diamino-t-butyl group, 1,2,3-triaminopropyl group,cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group,2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropylgroup, 2,3-dicyano-t-butyl group, 1,2,3-tricyanopropyl group,nitromethyl group, 1-nitroethyl group, 2-nitroethyl group,2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropylgroup, 2,3-dinitro-t-butyl group and 1,2,3-trinitropropyl group.

Examples of the divalent group forming a ring include tetramethylenegroup, pentamethylene group, hexamethylene group,diphenylmethan-2,2′-diyl group, diphenylethan-3,3′-diyl group anddiphenylpropan-4,4′-diyl group.

Examples of the halogen atom include fluorine, chlorine, bromine andiodine.

In general formula (1), a, b and c each represent an integer of 0 to 4and preferably 0 or 1.

n represents an integer of 1 to 3 and, when n represents 2 or 3, theplurality of groups in [ ] may be the same with or different from eachother.

Examples of the substituent in the groups represented by Ar, Ar′ and Xinclude halogen atoms, hydroxyl group, nitro group, cyano group, alkylgroups, aryl groups, cycloalkyl groups, alkoxyl groups, aromaticheterocyclic groups, aralkyl groups, aryloxyl groups, arylthio groups,alkoxycarbonyl groups and carboxyl group.

Examples of the anthracene derivative represented by general formula (1)of the present invention are shown in the following. However, theanthracene derivative represented by general formula (1) is not limitedto the compounds shown as the examples. In the following formulae, Merepresents methyl group, and Bu represents butyl group.

Among the anthracene derivatives represented by general formula (1),compounds represented by general formula (1) in which Ar and Ar′ bothrepresent naphthyl group and a=b=c=0 are preferable.

The anthracene derivative represented by general formula (2) of thepresent invention is a novel compound, which is included in the compoundrepresented by general formula (1).

In general formula (2), Ar represents a substituted or unsubstitutedcondensed aromatic group having 10 to 50 nuclear carbon atoms.

In general formula (2), Ar′ represents a substituted or unsubstitutedaromatic group having 6 to 50 nuclear carbon atoms.

In general formula (2), X represents a substituted or unsubstitutedaromatic group having 6 to 50 nuclear carbon atoms, a substituted orunsubstituted aromatic heterocyclic group having 5 to 50 nuclear atoms,a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,a substituted or unsubstituted alkoxyl group having 1 to 50 carbonatoms, a substituted or unsubstituted aralkyl group having 6 to 50carbon atoms, a substituted or unsubstituted aryloxyl group having 5 to50 nuclear atoms, a substituted or unsubstituted arylthio group having 5to 50 nuclear atoms, a substituted or unsubstituted alkoxycarbonyl grouphaving 1 to 50 carbon atoms, carboxyl group, a halogen atom, cyanogroup, nitro group or hydroxyl group.

Examples of the groups represented by Ar, Ar′ and X include the samegroups as the groups described as the examples of the correspondinggroups in general formula (1).

Examples of the substituent in the groups represented by Ar, Ar′ and Xinclude halogen atoms, hydroxyl group, nitro group, cyano group, alkylgroups, aryl groups, cycloalkyl groups, alkoxyl groups, aromaticheterocyclic groups, aralkyl groups, aryloxyl groups, arylthio groups,alkoxycarbonyl groups and carboxyl group.

In general formula (2), a and b each represent an integer of 0 to 4 andpreferably 0 or 1.

n represents an integer of 1 to 3 and, when n represents 2 or 3, theplurality of groups represented by the formula shown in [ ] may be thesame with or different from each other.

Examples of the anthracene derivative represented by general formula (2)include (AN1) to (AN4), (AN7) to (AN14), (AN17) to (AN24), (AN27) to(AN36), (AN39) to (AN43) and (AN46) to (AN48) among the compounds shownas the examples of the anthracene derivative represented by generalformula (1). However, anthracene derivative represented by generalformula (2) is not limited to the examples shown above.

It is preferable that the anthracene derivative represented by generalformula (2) of the present invention is used as the material for organicEL devices.

The anthracene derivative represented by general formula (1) or (2) ofthe present invention which is used for organic EL devices can besynthesized in accordance with a suitable combination of the Suzukicoupling reaction, the halogenation reaction and the boration reactionusing a halogenated anthracene derivative and a commercial arylboricacid, an arylboric acid synthesized in accordance with a known processor a derivative thereof as the starting materials. The reaction schemeis shown in the following.

Many reports are found on the Suzuki coupling reaction (Chem. Rev. Vol.95, No. 7, 2475 (1995) and others). The reaction can be conducted underthe conditions described in these reports.

The reaction is, in general, conducted under an inert atmosphere such asthe atmospheres of nitrogen, argon and helium and may be conducted undera pressurized condition, where necessary. The reaction temperature is inthe range of 15 to 300° C. and preferably in the range of 30 to 200° C.

As the solvent for the reaction, water, aromatic hydrocarbons such asbenzene, toluene and xylene, ethers such as 1,2-dimethoxyethane, diethylether, methyl t-butyl ether, tetrahydrofuran and dioxane; saturatedhydrocarbons such as pentane, hexane, heptane, octane and cyclohexane,halides such as dichloromethane, chloroform, carbon tetrachloride,1,2-dichloroethane and 1,1,1-trichloroethane, nitriles such asacetonitrile and benzonitrile, esters such as ethyl acetate, methylacetate and butyl acetate, and amides such as N,N-dimethylformamide,N,N-dimethylacetamide and N-methylpyrrolidone, can be used singly or asa mixture. Among these solvents, toluene, 1,2-dimethoxyethane, dioxaneand water are preferable. The amount by weight of the solvent is, ingeneral, in the range of 3 to 50 times as much as and preferably in therange of 4 to 20 times as much as the amount by weight of the arylboricacid or the derivative thereof.

Examples of the base used in the reaction include sodium carbonate,potassium carbonate, sodium hydroxide, potassium hydroxide, sodiumhydrogencarbonate, potassium hydrogencarbonate, magnesium carbonate,lithium carbonate, potassium fluoride, cesium fluoride, cesium chloride,cesium bromide, cesium carbonate, potassium phosphate, methoxysodium,t-butoxypotassium and t-butoxylithium. Among these bases, sodiumcarbonate is preferable. The amount of the salt is, in general, in therange of 0.7 to 10 mole equivalents and preferably in the range of 0.9to 6 mole equivalents based on the amount of the arylboric acid or thederivative thereof.

Examples of the catalyst used in the reaction include palladiumcatalysts such as tetrakis(triphenylphosphine)palladium,dichlorobis-(triphenylphosphine)palladium,dichloro[bis(diphenylphosphino)ethane]-palladium,dichloro[bis(diphenylphosphino)propane]palladium,dichloro-[bis(diphenylphosphino)butane]palladium anddichloro[bis(diphenyl-phosphino)ferrocene]palladium; and nickelcatalysts such as tetrakis-(triphenylphosphine)nickel,dichlorobis(triphenylphosphine)nickel,dichloro[bis(diphenylphosphino)ethane]nickel,dichloro[bis(diphenyl-phosphino)propane]nickel,dichloro[bis(diphenylphosphino)butane]nickel anddichloro[bis(diphenylphosphino)ferrocene]nickel. Among these catalysts,tetrakis(triphenylphosphine)palladium is preferable. The amount of thecatalyst is, in general, in the range of 0.001 to 1 mole equivalent andpreferable in the range of 0.01 to 0.1 mole equivalent based on theamount of the halogenated anthracene derivative.

Examples of the halogen in the halogenated anthracene derivative includeiodine atom, bromine atom and chlorine atom. Iodine atom and bromineatom are preferable.

The halogenating agent in the halogenation reaction is not particularlylimited. For example, N-halogenated succinimides are preferable. Theamount of the halogenating agent is, in general, in the range of 0.8 to10 mole equivalents and preferably in the range of 1 to 5 moleequivalents based on the amount of the anthracene derivative.

The reaction is, in general, conducted under an inert atmosphere suchthe atmospheres of nitrogen, argon and helium in an inert solvent.Examples of the inert solvent include N,N-dimethylformamide,N,N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, carbontetrachloride, chlorobenzene, dichlorobenzene, nitrobenzene, toluene,xylene, methylcellosolve, ethylcellosolve and water. Among thesesolvents, N,N-dimethylformamide and N-methylpyrrolidone are preferable.The amount by weight of the solvent is, in general, in the range of 3 to50 time as much as and preferably in the range of 5 to 20 times as muchas the amount by weight of the anthracene derivative. The reaction isconducted at a temperature in the range of 0 to 200° C. and preferablyin the range of 20 to 120° C.

The boration reaction can be conducted in accordance with a knownprocess (Jikken Kagaku Koza, 4^(th) edition, edited by the ChemicalSociety of Japan, Volume 24, Pages 61 to 90; J. Org. Chem. Vol. 60, 7508(1995); and others). For example, when the reaction contains thelithiation reaction or the Grignard reaction of a halogenated anthracenederivative, in general, the reaction is conducted under an inertatmosphere such as the atmospheres of nitrogen, argon and helium, and aninert solvent is used as the solvent. As the inert solvent, for example,a saturated hydrocarbon such as pentane, hexane, heptane, octane andcyclohexane, an ether such as 1,2-dimethoxyethane, diethyl ether, methylt-butyl ether, tetrahydrofuran and dioxane, or an aromatic hydrocarbonsuch as toluene and xylene, can be used singly or as a mixed solvent. Itis preferable that diethyl ether or toluene is used. The amount byweight of the solvent is, in general, in the range of 3 to 50 times asmuch as and preferably in the range of 4 to 20 times as much as theamount by weight of the halogenated anthracene derivative.

Examples of the lithiating agent include alkyl metal reagents such asn-butyllithium, t-butyllithium, phenyllithium and methyllithium; andamide bases such as lithium diisopropylamide and lithiumbistrimethylsilylamide. Among these agents, n-butyllithium ispreferable. The Grignard reagent can be prepared by the reaction of thehalogenated anthracene derivative and metallic magnesium. As thetrialkyl borate of the borating reagent, for example, trimethyl borate,triethyl borate, triisopropyl borate and tributyl borate can be used.Trimethyl borate and triisopropyl borate are preferable.

The amounts of the lithiating agent and the metallic magnesium are each,in general, in the range of 1 to 10 mole equivalents and preferably inthe range of 1 to 2 mole equivalents base on the amount of thehalogenated anthracene derivative. The amount of the trialkyl borate is,in general, in the range of 1 to 10 mole equivalents and preferably inthe range of 1 to 5 mole equivalents based on the amount of thehalogenated anthracene derivative. The reaction temperature is, ingeneral, in the range of −100 to 50° C. and preferably in the range of−75 to 10° C.

In the organic EL device of the present invention, it is preferable thatthe light emitting layer comprises the anthracene derivative representedby general formula (1) or (2) as the main component.

In the organic EL device of the present invention, it is preferable thatthe light emitting layer further comprises an arylamine compound and/ora styrylamine compound.

As the styrylamine compound, compounds represented by the followinggeneral formula (A):

wherein Ar₂ represent a group selected from phenyl group, biphenylgroup, terphenyl group, stilbene group and distyrylaryl groups, Ar₃ andAr₄ each represent hydrogen atom or an aromatic group having 6 to 20carbon atoms, the groups represented by Ar₂, Ar₃ and Ar₄ may besubstituted, p represents an integer of 1 to 4 and, preferably, at leastone of the groups represented by Ar₃ and Ar₄ is substituted with styrylgroup, are preferable.

Examples of the aromatic group having 6 to 20 carbon atoms includephenyl group, naphthyl group, anthranyl group, phenanthryl group andterphenyl group.

As the arylamine compound, compounds represented by the followinggeneral formula (B):

wherein Ar₅ to Ar₇ each represent an aryl group having 5 to 40 nuclearcarbon atoms, and q represents an integer of 1 to 4, are preferable.

Examples of the aryl group having 5 to 40 nuclear carbon atoms includephenyl group, naphthyl group, anthranyl group, phenanthryl group,pyrenyl group, coronyl group, biphenyl group, terphenyl group, pyrrolylgroup, furanyl group, thiophenyl group, benzothiophenyl group,oxadiazolyl group, diphenylanthranyl group, indolyl group, carbazolylgroup, pyridyl group, benzoquinolyl group, fluoranthenyl group,acenaphthofluoranthenyl group and stilbene group. Preferable examples ofthe substituent to the aryl group include alkyl groups having 1 to 6carbon atoms such as ethyl group, methyl group, i-propyl group, n-propylgroup, s-butyl group, t-butyl group, pentyl group, hexyl group,cyclopentyl group and cyclohexyl group; alkoxyl groups having 1 to 6carbon atoms such as ethoxyl group, methoxyl group, i-propoxyl group,n-propoxyl group, s-butoxyl group, t-butoxyl group, pentoxyl group,hexyloxyl group, cyclopentoxyl group and cyclohexyloxyl group; arylgroups having 5 to 40 nuclear atoms; amino groups substituted with anaryl group having 5 to 40 nuclear atoms; ester groups having an arylgroup having 5 to 40 nuclear atoms; ester groups having an alkyl grouphaving 1 to 6 carbon atoms; cyano group; nitro group; and halogen atoms.

The construction of the device in the organic EL device of the presentinvention will be described in the following.

Typical examples of the construction of the organic EL device include:

(1) An anode/a light emitting layer/a cathode;(2) An anode/a hole injecting layer/a light emitting layer/a cathode;(3) An anode/a light emitting layer/an electron injecting layer/acathode;(4) An anode/a hole injecting layer/a light emitting layer/an electroninjecting layer/a cathode;(5) An anode/an organic semiconductor layer/a light emitting layer acathode;(6) An anode/an organic semiconductor layer/an electron barrier layer/alight emitting layer/a cathode;(7) An anode/an organic semiconductor layer/a light emitting layer/anadhesion improving layer/a cathode;(8) An anode/a hole injecting layer/a hole transporting layer/a lightemitting layer/an electron injecting layer/a cathode;(9) An anode/an insulating layer/a light emitting layer/an insulatinglayer/a cathode;(10) An anode/an inorganic semiconductor layer/an insulating layer/alight emitting layer/an insulating layer/a cathode;(11) An anode/an organic semiconductor layer/an insulating layer/a lightemitting layer/an insulating layer/a cathode;(12) An anode/an insulating layer/a hole injecting layer/a holetransporting layer/a light emitting layer/an insulating layer/a cathode;and(13) An anode/an insulating layer/a hole injecting layer/a holetransporting layer/a light emitting layer/an electron injecting layer/acathode.

Among the above constructions, construction (8) is preferable. However,the construction of the organic EL device is not limited to those shownabove as the examples.

In general, the organic EL device is prepared on a substrate whichtransmits light. The substrate which transmits light is the substratewhich supports the organic EL device. It is preferable that thesubstrate which transmits light has a transmittance of light of 50% orgreater in the visible region of 400 to 700 nm. It is also preferablethat a flat and smooth substrate is used.

As the substrate which transmits light, for example, glass plates andsynthetic resin plates are advantageously used. Examples of the glassplate include plates made of soda lime glass, glass containing bariumand strontium, lead glass, aluminosilicate glass, borosilicate glass,barium borosilicate glass and quartz. Examples of the synthetic resinplate include plates made of polycarbonate resins, acrylic resins,polyethylene terephthalate resins, polyether sulfide resins andpolysulfone resins.

As the anode, an electrode made of a material such as a metal, an alloy,a conductive compound and a mixture of these materials which has a greatwork function (4 eV or more) is preferable. Specific examples of thematerial for the anode include metals such as An and conductivematerials such as CuI, ITO (indium tin oxide), SnO₂, ZnO and In—Zn—O.The anode can be prepared by forming a thin film of the electrodematerial described above in accordance with a process such as the vapordeposition process and the sputtering process. When the light emittedfrom the light emitting layer is obtained through the anode, it ispreferable that the anode has a transmittance of the emitted lightgreater than 10%. It is also preferable that the sheet resistivity ofthe anode is several hundred Ω/□ or smaller. The thickness of the anodeis, in general, selected in the range of 10 nm to 1 μm and preferably inthe range of 10 to 200 nm.

In the organic EL device of the present invention, it is preferable thata layer of a chalcogenide, a metal halide or a metal oxide (this layermay occasionally be referred to as a surface layer) is disposed on thesurface of at least one of the pair of electrodes prepared as describedabove. Specifically, it is preferable that a layer of a chalcogenide(including an oxide) of a metal such as silicon and aluminum is disposedon the surface of the anode at the side of the light emitting layer, anda layer of a metal halide or a metal oxide is disposed on the surface ofthe cathode at the side of the light emitting layer. Due to the abovelayers, stability in driving can be improved.

Preferable examples of the chalcogenide include SiO_(x) (1≦x≦2), AlO_(x)(1≦x≦1.5), SiON and SiALON. Preferable examples of the metal halideinclude LiF, MgF₂, CaF₂ and fluorides of rare earth metals. Preferableexamples of the metal oxide include Cs₂O, Li₂O, MgO, SrO, BaO and CaO.

In the organic EL device of the present invention, it is preferable thata mixed region of an electron transfer compound and a reducing dopant ora mixed region of a hole transfer compound and an oxidizing dopant isdisposed on the surface of at least one of the pair of electrodesprepared as described above. Due to the mixed region disposed asdescribed above, the electron transfer compound is reduced to form ananion, and injection and transportation of electrons from the mixedregion into the light emitting medium can be facilitated. The holetransfer compound is oxidized to form a cation, and injection andtransportation of holes from the mixed region into the light emittingmedium is facilitated. Preferable examples of the oxidizing dopantinclude various types of Lewis acid and acceptor compounds. Preferableexamples of the reducing dopant include alkali metals, compounds ofalkali metals, alkaline earth metals, rare earth metals and compounds ofthese metals.

In the organic EL device of the present invention, the light emittinglayer has the following functions:

(1) The injecting function: the function of injecting holes from theanode or the hole injecting layer and injecting electrons from thecathode or the electron injecting layer when an electric field isapplied;(2) The transporting function: the function of transporting injectedcharges (electrons and holes) by the force of the electric field; and(3) The light emitting function: the function of providing the field forrecombination of electrons and holes and leading the recombination tothe emission of light.

As the process for forming the light emitting layer, a conventionalprocess such as the vapor deposition process, the spin coating processand the LB process can be used. It is particularly preferable that thelight emitting layer is a molecular deposit film. The molecular depositfilm is a thin film formed by deposition of a material compound in thegas phase or a thin film formed by solidification of a material compoundin a solution or in the liquid phase. In general, the molecular depositfilm can be distinguished from the thin film formed in accordance withthe LB process (the molecular accumulation film) based on thedifferences in the aggregation structure and higher order structures andfunctional differences caused by these structural differences.

As disclosed in Japanese Patent Application Laid-Open No. Showa57(1982)-51781, the light emitting layer can also be formed bydissolving a binder such as a resin and the material compounds into asolvent to prepare a solution, followed by forming a thin film from theprepared solution in accordance with the spin coating process or thelike.

In the present invention, where desired, the light emitting layer maycomprise conventional light emitting materials other than the lightemitting material of the present invention, or a light emitting layercomprising other conventional light emitting material may be laminatedto the light emitting layer comprising the light emitting material ofthe present invention as long as the object of the present invention isnot adversely affected.

The hole injecting layer and the hole transporting layer are layerswhich help injection of holes into the light emitting layer andtransport the holes to the light emitting region. The layers exhibit agreat mobility of holes and, in general, have an ionization energy assmall as 5.5 eV or smaller. For the hole injecting layer and the holetransporting layer, a material which transports holes to the lightemitting layer at a small strength of the electric field is preferable.A material which exhibits, for example, a mobility of holes of at least10⁻⁶ cm²/V·sec under application of an electric field of 10⁴ to 10⁶ V/cmis preferable. A material can be selected as desired from materialswhich are conventionally used as the charge transporting material ofholes in photoconductive materials and conventional materials which areused for the hole injecting layer in organic EL devices.

To form the hole injecting layer or the hole transporting layer, a thinfilm may be formed from the material for the hole injecting layer or thehole transporting layer, respectively, in accordance with conventionalprocess such as the vacuum vapor deposition process, the spin coatingprocess, the casting process and the LB process. The thickness of thehole injecting layer and the hole transporting layer is not particularlylimited. In general, the thickness is 5 nm to 6 μm.

The electron injection layer and the electron transporting layer arelayers which help injection of electrons into the light emitting layer,transport electrons to the light emitting region and exhibit a greatmobility of electrons. The adhesion improving layer is a layer made of amaterial exhibiting excellent adhesion with the cathode among theelectron injecting layers. As the material for the electron injectinglayer, metal complexes of 8-hydroxyquinoline and derivatives thereof arepreferable. Examples of the metal complex of 8-hydroxyquinoline andderivatives thereof include metal chelates of oxinoid compoundsincluding chelates of oxine (in general, 8-quinolinol or8-hydroxyquinoline). For example, tris(8-quinolinol)aluminum can be usedas the electron injecting material.

In general, an organic EL device tends to form defects in pixels due toleak and short circuit since an electric field is applied to ultra-thinfilms. To prevent the formation of the defects, a layer of an insulatingthin film may be inserted between the pair of electrodes.

Examples of the material used for the insulating layer include aluminumoxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide,magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride,aluminum nitride, titanium oxide, silicon oxide, germanium oxide,silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide andvanadium oxide. Mixtures and laminates of the above compounds can alsobe used.

To prepare the organic EL device of the present invention, for example,the anode, the light emitting layer and, where necessary, the holeinjecting layer and the electron injecting layer are formed inaccordance with the above processes using the above materials, and thecathode is formed in the last step. The organic EL device may beprepared by forming the above layers in the order reverse to thatdescribed above, i.e., the cathode being formed in the first step andthe anode in the last step.

An embodiment of the process for preparing an organic EL device having aconstruction in which an anode, a hole injecting layer, a light emittinglayer, an electron injecting layer and a cathode are disposedsuccessively on a substrate transmitting light will be described in thefollowing.

On a suitable substrate transmitting light, a thin film made of amaterial for the anode is formed in accordance with the vapor depositionprocess or the sputtering process so that the thickness of the formedthin film is 1 μm or smaller and preferably in the range of 10 to 200nm. The formed thin film is used as the anode. Then, a hole injectinglayer is formed on the anode. The hole injecting layer can be formed inaccordance with the vacuum vapor deposition process, the spin coatingprocess, the casting process or the LB process, as described above. Thevacuum vapor deposition process is preferable since a uniform film canbe easily obtained and the possibility of formation of pin holes issmall. When the hole injecting layer is formed in accordance with thevacuum vapor deposition process, in general, it is preferable that theconditions are suitably selected in the following ranges: thetemperature of the source of the deposition: 50 to 450° C.; the vacuum:10⁻⁷ to 10⁻³ Torr; the rate of deposition: 0.01 to 50 nm/second; thetemperature of the substrate: −50 to 300° C. and the thickness of thefilm: 5 nm to 5 μm; although the conditions of the vacuum vapordeposition are different depending on the used compound (the materialfor the hole injecting layer) and the crystal structure and therecombination structure of the hole injecting layer to be formed.

Then, the light emitting layer is formed on the hole injecting layerformed above. Using the light emitting material described in the presentinvention, a thin film of the light emitting material can be formed inaccordance with the vacuum vapor deposition process, the sputteringprocess, the spin coating process or the casting process, and the formedthin film is used as the light emitting layer. The vacuum vapordeposition process is preferable because a uniform film can be easilyobtained and the possibility of formation of pin holes is small. Whenthe light emitting layer is formed in accordance with the vacuum vapordeposition process, in general, the conditions of the vacuum vapordeposition process can be selected in the same ranges as those describedfor the vacuum vapor deposition of the hole injecting layer although theconditions are different depending on the used compound. It ispreferable that the thickness is in the range of 10 to 40 nm.

An electron injecting layer is formed on the light emitting layer formedabove. Similarly to the hole injecting layer and the light emittinglayer, it is preferable that the electron injecting layer is formed inaccordance with the vacuum vapor deposition process since a uniform filmmust be obtained. The conditions of the vacuum vapor deposition can beselected in the same ranges as those described for the vacuum vapordeposition of the hole injecting layer and the light emitting layer.

A cathode is formed on the electron injecting layer formed above in thelast step, and an organic EL device can be obtained. The cathode is madeof a metal and can be formed in accordance with the vacuum vapordeposition process or the sputtering process. It is preferable that thevacuum vapor deposition process is used in order to prevent formation ofdamages on the lower organic layers during the formation of the film.

In the above preparation of the organic EL device, it is preferable thatthe above layers from the anode to the cathode are formed successivelywhile the preparation system is kept in a vacuum after being evacuated.

The organic EL device which can be prepared as described above emitslight when a direct voltage of 3 to 40 V is applied in the conditionthat the anode is connected to a positive electrode (+) and the cathodeis connected to a negative electrode (−). When the connection isreversed, no electric current is observed and no light is emitted atall. When an alternating voltage is applied to the organic EL device,the uniform light emission is observed only in the condition that thepolarity of the anode is positive and the polarity of the cathode isnegative. When an alternating voltage is applied to the organic ELdevice, any type of wave shape can be used.

The present invention will be described more specifically with referenceto examples in the following. However, the present invention is notlimited to the examples.

Example 1 (Synthesis of 10-(2-naphthyl)anthracene-9-boric acid)

Under the atmosphere of argon, a solution prepared by dissolving 549 gof 2-naphthaleneboric acid (manufactured by TOKYO KASEI Co., Ltd.), 684g of 9-bromoanthracene (manufactured by TOKYO KASEI Co., Ltd.), 61.5 gof tetrakis(triphenylphosphine)palladium(0) (manufactured by TOKYO KASEICo., Ltd.), 4.9 liters of toluene (manufactured by HIROSHIMA WAKO Co.,Ltd.) and 845.9 g of sodium carbonate (manufactured by HIROSHIMA WAKOCo., Ltd.) into 4.9 liters of water was placed into a 20 liter flask,and the resultant mixture was stirred for 24 hours while being heatedunder the refluxing condition. After the reaction was completed, thereaction mixture was cooled to the room temperature, and formed crystalswere separated by filtration. The obtained crystals were recrystallizedfrom toluene, and 751 g of crystals were obtained

Under the atmosphere of argon, 750 g of the crystals obtained above and10 liters of dehydrated dimethylformamide (DMF) (manufactured byHIROSHIMA WAKO Co., Ltd.) were placed into a 20 liter flask, and theresultant mixture was heated at 80° C. After the material was dissolved,482.4 g of N-bromosuccinimide (manufactured by HIROSHIMA WAKO Co., Ltd.)was added at 50° C., and the resultant mixture was stirred for 2 hours.After the reaction was completed, the reaction solution was poured into20 liters of purified water, and formed crystals were separated byfiltration. The separated crystals were recrystallized from toluene, and689 g of crystals were obtained.

Under the atmosphere of argon, 588 g of the crystals obtained above, 4.5liters of dehydrated ether (manufactured by HIROSHIMA WAKO Co., Ltd.)and 4.5 liters of dehydrated toluene (manufactured by HIROSHIMA WAKOCo., Ltd.) Were placed into a 20 liter flask, and the resultant mixturewas cooled at −64° C. in a dry ice bath. To the cooled mixture, 1.2liters of a 1.6 M hexane solution of butyllithium (manufactured byHIROSHIMA WAKO Co., Ltd.) was added dropwise over 30 minutes, and thereaction was allowed to proceed at −64° C. for 2 hours. To the resultantreaction mixture, 866 g of triisopropyl borate (manufactured by TOKYOKASEI Co., Ltd.) was added dropwise over 20 minutes. After the additionwas completed, the temperature was adjusted at the room temperature, andthe reaction mixture was stirred for 12 hours. After the resultantreaction mixture was cooled with ice, 4 liters of 2 N hydrochloric acidwas added at a temperature of 10° C. or lower, and 1 liter of toluenewas added. The organic phase separated from the resultant mixture wasdried with sodium sulfate and concentrated under a reduced pressure.Hexane was added to the resultant solution, and formed crystals wereseparated by filtration. The obtained crystals were dissolved into 5liters of tetrahydrofuran. To the resultant solution, 500 ml ofconcentrated hydrochloric acid and 5 g of tetrabutylammonium bromidewere added, and the resultant mixture was stirred for 12 hours. Theformed crystals were separated by filtration and dried, and 431 g ofcrystals were obtained.

Since m/z=348 in the field desorption mass analysis (FD-MS) of theobtained compound, which corresponded to C₂₄H₁₇BO₂=348, the compound wasidentified to be 10-(2-naphthyl)anthracene-9-boric acid (the yield:47%).

Synthesis Example 2 (Synthesis of 2-(4-bromophenyl)naphthalene)

Under the atmosphere of argon, a solution prepared by dissolving 7.1 gof 2-naphthaleneboric acid (manufactured by TOKYO KASEI Co., Ltd.), 12.9g of 4-iodobromobenzene (manufactured by TOKYO KASEI Co., Ltd.), 0.6 gof tetrakis(triphenylphosphine)palladium (0) (manufactured by TOKYOKASEI Co., Ltd.) and 12.7 g of sodium carbonate (manufactured byHIROSHIMA WAKO Co, Ltd.) into 60 ml of water was placed into a 300 mlflask, and the resultant mixture was stirred for 24 hours while beingheated under the refluxing condition. After the reaction was completed,the reaction mixture was cooled to the room temperature, and formedcrystals were separated by filtration. The obtained crystals wererecrystallized from toluene, and 9.0 g of crystals were obtained

Since m/z=284 in FD-MS of the obtained compound, which corresponded toC₁₆H₁₁Br=283, the compound was identified to be2-(4-bromophenyl)naphthalene (the yield: 77%).

Synthesis Example 3 (Synthesis of 3-(4-bromophenyl)fluoranthene)

Under the atmosphere of argon, 62 g of fluoranthene and 250 ml ofdehydrated DMF (manufactured by HIROSHIMA WAKO Co., Ltd.) were placedinto a 500 ml flask and heated at 80° C. After the material wasdissolved, 60 g of N-bromosuccinimide (manufactured by HIROSHIMA WAKOCo., Ltd.) was added at 50° C., and the resultant mixture was stirredfor 2 hours. After the reaction was completed, the reaction solution waspoured into 500 ml of purified water, and formed, crystals wereseparated by filtration. The separated crystals were purified inaccordance with the column chromatography, and 10.5 g of crystals wereobtained.

Under the atmosphere of argon, 10.0 g of the crystals obtained above,120 ml of dehydrated ether (manufactured by HIROSHIMA WAKO Co., Ltd.)and 120 ml of dehydrated toluene (manufactured by HIROSHIMA WAKO Co.,Ltd.) were placed into a 500 ml flask, and the resultant mixture wascooled at −0.64° C. in a dry ice bath. To the cooled mixture, 25 ml of a1.6 M hexane solution of butyllithium (manufactured by HIROSHIMA WAKOCo., Ltd.) was added dropwise over 30 minutes, and the reaction wasallowed to proceed at −64° C. for 2 hours. To the resultant reactionmixture, 8 g of triisopropyl borate (manufactured by TOKYO KASEI Co.,Ltd.) was added dropwise over 20 minutes. After the addition wascompleted, the temperature was adjusted at the room temperature, and thereaction mixture was stirred for 12 hours. After the resultant reactionmixture was cooled with ice, 100 ml of 2 N hydrochloric acid was addedat a temperature of 10° C. or lower, and 25 ml of toluene was added. Theorganic phase separated from the resultant mixture was dried with sodiumsulfate and concentrated under a reduced pressure. Hexane was added tothe resultant solution, and formed crystals were separated byfiltration. The obtained crystals were dissolved into 120 nil oftetrahydrofuran. To the resultant solution, 15 ml of concentratedhydrochloric acid and 0.15 g of tetrabutylammonium bromide were added,and the resultant mixture was stirred for 12 hours. The formed crystalswere separated by filtration and dried, and 7.0 g of crystals of3-fluorantheneboric acid were obtained.

Under the atmosphere of argon, a solution prepared by dissolving 7.0 gof the crystals obtained above (manufactured by TOKYO KASEI Co., Ltd.),9.0 of 4-iodobromobenzene (manufactured by TOKYO KASEI Co., Ltd.), 0.6 gof tetrakis(triphenylphosphine)palladium(0) (manufactured by TOKYO KASEICo., Ltd.) and 12.7 g of sodium carbonate (manufactured by HIROSHIMAWAKO Co., Ltd.) into 60 ml of water was placed into a 300 ml flask, andthe resultant mixture was stirred for 24 hours while being heated underthe refluxing condition. After the reaction was completed, the reactionmixture was cooled to the room temperature, and formed crystals wereseparated by filtration. The obtained crystals were recrystallized fromtoluene, and 6.4 g of crystals were obtained

Since m/z=358 and 356 in FD-MS of the obtained compound, whichcorresponded to C₂₂H₁₅Br=357, the compound was identified to be3-(4-bromophenyl)fluoranthene (the yield: 6%).

Synthesis Example 4 (Synthesis of 10-(3-fluoranthenyl)anthracene-9-boricacid

Under the atmosphere of argon, a solution prepared by dissolving 7.85 gof 3-fluorantheneboric acid, 6.84 g of 9-bromoanthracene (manufacturedby TOKYO KASEI Co., Ltd.), 0.6 g oftetrakis-(triphenylphosphine)palladium(0) (manufactured by TOKYO KASEICo., Ltd.), 50 ml of toluene (manufactured by HIROSHIMA WAKO Co., Ltd.)and 8.5 g of sodium carbonate (manufactured by HIROSHIMA WAKO Co., Ltd.)into 50 ml of water was placed into a 300 ml flask, and the resultantmixture was stirred for 24 hours while being heated under the refluxingcondition. After the reaction was completed, the reaction mixture wascooled to the room temperature, and formed crystals were separated byfiltration. The obtained crystals were recrystallized from toluene, and4.6 g of crystals were obtained

Under the atmosphere of argon, 4.5 g of the crystals obtained above and100 ml of dehydrated DMF (manufactured by HIROSHIMA WAKO Co., Ltd.) wereplaced into a 300 ml flask, and the resultant mixture was heated at 80°C. After the material was dissolved, 2.3 g of N-bromosuccinimide(manufactured by HIROSHIMA WAKO Co., Ltd.) was added at 50° C., and theresultant mixture was stirred for 2 hours. After the reaction wascompleted, the reaction solution was poured into 200 ml of purifiedwater, and formed crystals were separated by filtration. The separatedcrystals were recrystallized from toluene, and 4.5 g of crystals wereobtained.

Under the atmosphere of argon, 4.5 g of the crystals obtained above, 50ml of dehydrated ether (manufactured by HIROSHIMA WAKO Co., Ltd.) and 50ml of dehydrated toluene (manufactured by HIROSHIMA WAKO Co., Ltd.) wereplaced into a 300 ml flask, and the resultant mixture was cooled at −64°C. in a dry ice bath. To the cooled mixture, 7 ml of a 1.6 M hexanesolution of butyllithium (manufactured by HIROSHIMA WAKO Co., Ltd.) wasadded dropwise over 30 minutes, and the reaction was allowed to proceedat −64° C. for 2 hours. To the resultant reaction mixture, 5.6 g oftriisopropyl borate (manufactured by TOKYO KASEI Co., Ltd.) was addeddropwise over 20 minutes. After the addition was completed, thetemperature was adjusted at the room temperature, and the reactionmixture was stirred for 12 hours. After the resultant reaction mixturewas cooled with ice, 40 ml of 2 N hydrochloric acid was added at atemperature of 10° C. or lower, and 10 ml of toluene was added. Theorganic phase separated from the resultant mixture was dried with sodiumsulfate and concentrated under a reduced pressure. Hexane was added tothe resultant solution, and formed crystals were separated byfiltration. The obtained crystals were dissolved into 50 ml oftetrahydrofuran. To the resultant solution, 5 ml of concentratedhydrochloric acid and 0.1 g of tetrabutylammonium bromide were added,and the resultant mixture was stirred for 12 hours. The formed crystalswere separated by filtration and dried, and 3.6 g of crystals wereobtained.

Since m/z=422 in FD-MS of the obtained compound, which corresponded toC₃₀H₁₉BO₂=422, the compound was identified to be10-(3-fluoranthenyl)anthracene-9-boric acid (the yield: 32%).

Synthesis Example 5 (Synthesis of 1-(4-bromophenyl)naphthalene)

The same procedures as those conducted in Synthesis Example 2 wereconducted except that 1-naphthaleneboric acid was used in place of2-naphthaleneboric acid, and 29.9 g of a colorless oily substance wasobtained.

Since m/z=284 and 282 in FD-MS of the obtained compound, whichcorresponded to C₁₆H₁₁Br=283, the compound was identified to be1-(4-bromophenyl)naphthalene (the yield: 88%).

Synthesis Example 6 (Synthesis of 2-(3-bromophenyl)naphthalene)

The same procedures as those conducted in Synthesis Example 2 wereconducted except that 3-iodobromobenzene was used in place of4-iodobromobenzene, and 20.1 g of a colorless oily substance wasobtained.

Since m/z=284 and 282 in FD-MS of the obtained compound, whichcorresponded to C₁₆H₁₁Br=283, the compound was identified to be2-(3-bromophenyl)naphthalene (the yield: 75%).

Example 1 (Synthesis of a Compound (AN8))

Under the atmosphere of argon, a solution prepared by dissolving 5.98 gof 10-(2-naphthyl)anthracene-9-boric acid obtained in Synthesis Example1, 4.05 g of 2-(4-bromophenyl)naphthalene obtained in Synthesis Example2, 0.33 g of tetrakis(triphenylphosphine)palladium(0) (manufactured byTOKYO KASEI Co., Ltd.), 60 ml of 1,2-dimethoxyethane (manufactured byHIROSHIMA WAKO Co., Ltd.) and 4.55 g of sodium carbonate (manufacturedby HIROSHIMA WAKO Co., Ltd.) into 21 ml of water was placed into a 300ml flask, and the resultant mixture was stirred for 24 hours while beingheated under the refluxing condition. After the reaction was completed,the reaction mixture was cooled to the room temperature, and formedcrystals were separated by filtration. The obtained compound waspurified in accordance with the column chromatography, and 3.4 g of alight yellow solid substance was obtained

Since m/z=506 in FD-MS of the obtained compound, which corresponded toC₄₀H₂₆=506, the compound was identified to be AN8 (the yield: 47%).

Example 2 (Synthesis of a Compound (AN10))

Under the atmosphere of argon, a solution prepared by dissolving 5.98 gof 10-(2-naphthyl)anthracene-9-boric acid obtained in Synthesis Example1, 5.13 g of 3-(4-bromophenyl)fluoranthene obtained in Synthesis Example3, 0.33 g of tetrakis(triphenylphosphine)palladium(0) (manufactured byTOKYO KASEI Co., Ltd.), 60 ml of 1,2-dimethoxyethane (manufactured byHIROSHIMA WAKO Co., Ltd.) and 4.55 g of sodium carbonate (manufacturedby HIROSHIMA WAKO Co., Ltd.) into 21 ml of water was placed into a 300ml flask, and the resultant mixture was stirred for 24 hours while beingheated under the refluxing condition. After the reaction was completed,the reaction mixture was cooled to the room temperature, and formedcrystals were separated by filtration. The obtained compound werepurified in accordance with the column chromatography, and 3.3 g of alight yellow solid substance was obtained

Since m/z=580 in FD-MS of the obtained compound, which corresponded toC₄₆H₂₈=580, the compound was identified to be AN10 (the yield: 40%).

Example 3 (Synthesis of a Compound (AN28))

Under the atmosphere of argon, a solution prepared by dissolving 7.24 gof 10-(3-fluoranthenyl)anthracene-9-boric acid obtained in SynthesisExample 4, 4.05 g of 2-(4-bromophenyl)naphthalene obtained in SynthesisExample 2, 0.33 g of tetrakis(triphenylphosphine)palladium(0)(manufactured by TOKYO KASEI Co., Ltd.), 60 ml of 1,2-dimethoxyethane(manufactured by HIROSHIMA WAKO Co., Ltd.) and 4.55 g of sodiumcarbonate (manufactured by HIROSHIMA WAKO Co., Ltd.) into 21 ml of waterwas placed into a 300 ml flask, and the resultant mixture was stirredfor 24 hours while being heated under the refluxing condition. After thereaction was completed, the reaction mixture was cooled to the roomtemperature, and formed crystals were separated by filtration. Theobtained compound was purified in accordance with the columnchromatography, and 3.6 g of a light yellow solid substance was obtained

Since m/z=580 in FD-MS of the obtained compound, which corresponded toC₄₆H₂₈=580, the compound was identified to be AN28 (the yield: 43%).

Example 4 (Synthesis of a Compound (AN30))

Under the atmosphere of argon, a solution prepared by dissolving 7.24 gof 10-(3-fluoranthenyl)anthracene-9-boric acid obtained in SynthesisExample 4, 5.13 g of 3-(4-bromophenyl)fluoranthene obtained in SynthesisExample 3, 0.33 g of tetrakis(triphenylphosphine)palladium(0)(manufactured by TOKYO KASEI Co., Ltd.), 60 ml of 1,2-dimethoxyethane(manufactured by HIROSHIMA WAKO Co., Ltd.) and 4.55 g of sodiumcarbonate (manufactured by HIROSHIMA WAKO Co., Ltd.) into 21 ml of waterwas placed into a 300 ml flask, and the resultant mixture was stirredfor 24 hours while being heated under the refluxing condition. After thereaction was completed, the reaction mixture was cooled to the roomtemperature, and formed crystals were separated by filtration. Theobtained compound was purified in accordance with the columnchromatography, and 3.1 g of a light yellow solid substance was obtained

Since m/z=654 in FD-MS of the obtained compound, which corresponded toC₅₂H₃₀=654, the compound was identified to be AN30 (the yield: 33%).

Example 5 (Preparation of an Organic EL Device)

A glass substrate (manufactured by GEOMATEC Company) of 25 mm×75 mm×1.1mm thickness having an ITO transparent electrode was cleaned byapplication of ultrasonic wave in isopropyl alcohol for 5 minutes andthen by exposure to ozone generated by ultraviolet light for 30 minutes.The glass substrate having the transparent electrode lines which hadbeen cleaned was attached to a substrate holder of a vacuum vapordeposition apparatus. On the surface of the cleaned substrate at theside having the transparent electrode, a film ofN,N′-bis(N,N′-diphenyl-4-aminophenyl)-N,N-diphenyl-4,4′-diamino-1,1′-biphenylshown below (referred to as a film of TPD232, hereinafter) having athickness of 60 nm was formed in a manner such that the formed filmcovered the transparent electrode. The formed film of TPD232 worked asthe hole injecting layer. On the formed film of TPD232, a film ofN,N,N′,N′-tetra (4-biphenyl)diaminobiphenylene shown below (referred toas a film of TBDB, hereinafter) having a thickness of 20 nm was formed.The formed film of TBDB worked as the hole transporting layer. On theformed film of TBDB, a film of the compound AN8 as the light emittingmaterial having a thickness of 40 nm was formed by vapor deposition. Atthe same time, an amine compound D1 having styryl group which is shownbelow was vapor deposited as the light emitting material in an amountsuch that the relative amounts by weight of AN8:D1 was 40:2. The formedfilm worked as the light emitting layer. On the film formed above, afilm of Alq shown below having a thickness of 10 nm was formed. The filmof Alq worked as the electron injecting layer. Thereafter, Li (thesource of lithium: manufactured by SAES GETTERS Company) as the reducingdopant and Alq were binary vapor deposited, and an Alq:Li film (thethickness: 10 nm) was formed as the electron injecting layer (cathode).On the formed Alq:Li film, metallic aluminum was vapor deposited to forma metal cathode, and an organic EL device was prepared.

Using the obtained organic EL device, the efficiency of light emissionand the half life at an initial luminance of 1,000 nit under theordinary environment of the use were measured. The results are shown inTable 1.

Examples 6 to 8 (Preparation of Organic EL Devices)

Organic EL devices were prepared in accordance with the same proceduresas those conducted in Example 5 except that compounds shown in Table 1were used as the light emitting material in place of AN8, and theefficiency of light emission and the half life at an initial luminanceof 1,000 nit under the ordinary environment of the use were measured.The results are shown in Table 1.

Example 9 (Preparation of an Organic EL Device)

An organic EL device was prepared in accordance with the same proceduresas those conducted in Example 5 except that an aromatic amine D2 shownbelow was used as the light emitting material in place of the aminecompound having styryl group D1, and the efficiency of light emissionand the half life at an initial luminance of 1,000 nit under theordinary environment of the use were measured. The results are shown inTable 1.

Example 10 (Synthesis of a Compound (AN5))

The same procedures as those conducted in Example 1 were conductedexcept that 3,5-diphenylbromobenzene was used in place of2-(4-bromophenyl)naphthalene, and 5.6 g of a light yellow solidsubstance was obtained.

Since m/z=532 in FD-MS of the obtained compound, which corresponded toC₄₂H₂₈Br=532, the compound was identified to be AN5 (the yield: 45%).

Example 11 (Synthesis of a Compound (AN7))

The same procedures as those conducted in Example 1 were conductedexcept that 1-(4-bromophenyl)naphthalene was used in place of2-(4-bromophenyl)naphthalene, and 7.8 g of a light yellow solidsubstance was obtained.

Since m/z=506 in FD-MS of the obtained compound, which corresponded toC₄₀H₂₆Br=506, the compound was identified to be AN7 (the yield: 54%).

Example 12 (Synthesis of a Compound (AN49))

The same procedures as those conducted in Example 1 were conductedexcept that 2-(3-bromophenyl)naphthalene was used in place of2-(4-bromophenyl)naphthalene, and 6.9 g of a light yellow solidsubstance was obtained.

Since m/z=506 in FD-MS of the obtained compound, which corresponded toC₄₀H₂₆Br=506, the compound was identified to be AN49 (the yield: 52%).

Examples 13 to 15 (Preparation of Organic EL Devices)

Organic EL devices were prepared in accordance with the same proceduresas those conducted in Example 5 except that compounds shown in Table 1were used as the light emitting material in place of AN8, and theefficiency of light emission and the half life at an initial luminanceof 1,000 nit under the ordinary environment of the use were measured.The results are shown in Table 1.

Comparative Example 1 (Preparation of an Organic EL Device)

An organic EL device was prepared in accordance with the same proceduresas those conducted in Example 5 except that an1 shown below was used asthe light emitting material in place of AN8, and the efficiency of lightemission and the half life at an initial luminance of 1,000 nit underthe ordinary environment of the use were measured. The results are shownin Table 1.

Comparative Example 2 (Preparation of an Organic EL Device)

An organic EL device was prepared in accordance with the same proceduresas those conducted in Example 5 except that an2 shown below was used asthe light emitting material in place of AN8, and the efficiency of lightemission and the half life at an initial luminance of 1,000 nit underthe ordinary environment of the use were measured. The results are shownin Table 1.

TABLE 1 Efficiency Compounds of of light Color of light emittingemission Half life emitted layer (cd/A) (hour) light Example 5 AN8/D111.2 4,200 blue Example 6 AN10/D1 11.0 4,000 blue Example 7 AN28/D1 10.93,700 blue Example 8 AN30/D1 10.8 3,700 blue Example 9 AN8/D2 10.6 3,200blue Example 13 AN5/D1 11.0 2,200 blue Example 14 AN7/D1 11.3 4,500 blueExample 15 AN49/D1 11.3 4,500 blue Comparative an1/D1 9.0 2,200 blueExample 1 Comparative an2/D1 8.8 1,100 blue Example 2

As shown in Table 1, the organic EL devices of Examples 5 to 9 and 13 to15 exhibited great efficiencies of light emission and had very longlives. In contrast, the organic EL devices of Comparative Examples 1 and2 exhibited small efficiencies of light emission and had short lives.

INDUSTRIAL APPLICABILITY

As described in detail in the above, the organic EL device of thepresent invention and the organic EL device using the anthracenederivative of the present invention exhibit great efficiencies of lightemission, have long lives and, therefore, are advantageously used as theorganic EL device which is considered to be used continuously for a longtime.

1-7. (canceled)
 8. An organic electroluminescence device whichcomprises: a cathode, an anode and an organic thin film layer disposedbetween the cathode and the anode, wherein: the organic thin film layercomprises at least one layer which comprises a light emitting layer; thelight emitting layer comprises a host and a dopant; the host is at leastone anthracene derivative of formula (2):

wherein: Ar is an unsubstituted 1-naphthyl group or an unsubstituted2-naphthyl group: Ar′ is an unsubstituted 1-naphthyl group or anunsubstituted 2-naphthyl group; a is 0; b is 0; n is 1; and the dopantis at least one arylamine compound of formula (B):

wherein: Ar₅ to Ar₇ are each independently a substituted orunsubstituted aryl group having 5 to 40 nuclear carbon atoms; and q isan integer of 1 to
 4. 9-12. (canceled)
 13. The organicelectroluminescence device according to claim 8, wherein q is
 2. 14. Theorganic electroluminescence device according to claim 8, wherein Ar₅ isa pyrenyl group.
 15. The organic electroluminescence device according toclaim 8, wherein Ar₆ and Ar₇ are each independently a phenyl group or anaphthyl group.
 16. The organic electroluminescence device according toclaim 8, wherein the substituent of Ar₅ to Ar₇ is independently an alkylgroup having 1 to 6 carbon atom or a phenyl group.
 17. The organicelectroluminescence device according to claim 8, wherein: q is 2; Ar₅ isa pyrenyl group; Ar₆ and Ar₇ are each independently a phenyl group or anaphthyl group; and the substituent of Ar₅ to Ar₇ is independently analkyl group having 1 to 6 carbon atom or a phenyl group.